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A method for synthesis of cis-4-hydroxyproline analogs is described. A cis epoxide is converted into a cis-4-hydroxyproline, while the trans epoxide is converted into a ketone or a-aminolactone in the presence of Lewis and Brønsted acids. We propose the divergent chemoselectivity is controlled by H-bonding within the cis epoxide.more » « lessFree, publicly-accessible full text available May 14, 2026
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